Propionic anhydride → CID 367964

HRID 1955702Notes

Reaction equation

HRID 1955702 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:14]C(=O)CC)(=[O:13])[CH2:11][CH3:12].C([O-])(=O)CC.[Na+]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:11]([CH3:12])[C:10]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 31263Propionic anhydrideHCID 680234-FluorobenzaldehydeHCID 2723816Sodium Propionate

Product 1

HCID 367964CID 367964

Procedure

p-Fluorobenzaldehyde (200 g, 1.61 mol), propionic anhydride (3.5 g, 2.42 mol) and sodium propionate (155 g, 1.61 mol) are mixed in a 1 l three-necked flask which had been flushed with nitrogen. The flask is heated gradually in an oil-bath to 140°. After 20 h, the flask is cooled to 100°and poured into 8 l of water. The precipitate is dissolved by adding potassium hydroxide (302 g) in 2 l of water. The aqueous solution is extracted with ether, and the ether extracts washed with potassium hydroxide solution. The combined aqueous layers are filtered, are acidified with concentrated HCl, and are filtered. The collected solid, p-fluoro-α-methylcinnamic acid, is washed with water, and is dried and used as obtained.

Workup

  1. customhad been flushed with nitrogen
  2. temperatureThe flask is heated gradually in an oil-bath to 140°
  3. temperaturethe flask is cooled to 100°and
  4. additionpoured into 8 l of water
  5. dissolutionThe precipitate is dissolved
  6. additionby adding potassium hydroxide (302 g) in 2 l of water
  7. extractionThe aqueous solution is extracted with ether
  8. washthe ether extracts washed with potassium hydroxide solution
  9. filtrationThe combined aqueous layers are filtered
  10. filtrationare filtered
  11. washThe collected solid, p-fluoro-α-methylcinnamic acid, is washed with water
  12. customis dried
  13. customas obtained

Sources & evidence

ORD record
ord-5bd568d7b8ef45188f3879f3618b8700
Source dataset
uspto-grants-1998_07
Patent number
US05776962

Reaction notes

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